Headless Horseman (2007)

Headless Horseman is a success in the sense that several heads are chopped off. Since this is a simply a slasher movie dressed up in a dark cloak and jack-o-lantern, it isn’t just the Headless Horseman whacking away with a sword or an axe. There’s also a person who falls into a bear trap headfirst as well as a guy hiding in the trunk of a car and the Horseman just jumps on the hatch while the guy’s head is sticking out of it. And if that sounds like an improvement over the musty old folk tale we all know, just wait until you see Headless cruising around on a motorcycle!

But while HH no doubt had a good time straddling his hog, the film’s failures in virtually every other aspect besides his pretty solid murderous rampage will leave you feeling like he left supernatural tire marks on your head.

As in most standard slasher movies, the audience is put in the uncomfortable position of enjoying each nasty killing because the characters being stalked are all the same variation of the same stupid, whiny college brats who are so irritating, you get mad that HH has to wait 20-30 minutes between kills.

There’s a whopping seven such young pukes here. There were three girls who you could tell apart because one wore glasses, one was a vapid airhead and one was going to survive. There are four boys and I could never keep straight which pasty-faced guy was the nerd and which one wasn’t. I also couldn’t remember which dark haired skinny guy was which, but one of them was the one killed in the car trunk early on which helped clear that up.

Trying to get to a Halloween party, the gang takes a shortcut that brings them to the cursed town of Wormwood. You immediately have no sympathy for them as the “shortcut” turns into them going from a highway to a dirt road that you can barely see for all the woods around it. Any normal person would have turned around, if for nothing else to avoid damaging their vehicle.

Then once they blow out a tire on a bear trap, they accept help from a sexy local girl who just happens to drive up in a tow truck and whose daddy runs the local car repair shop. Proving that none of them have ever watched a backwoods slasher movie before, they see it as a lucky break instead of the obvious ruse it truly is. (The guys can maybe be forgiven for not realizing this since the local gal is dressed like Daisy Duke, but what’s the girls’ excuse?)

Once in town, the film shifts into the expected anti small town bias these movies always delight in showcasing. With its dirty, run down buildings all bunched together on a single street, it doesn’t resemble a real small town so much as a movie set designed by folks who have always lived in big cities. Even more obnoxious is that all its inhabitants are dressed in ratty brown and grey clothes like they all went shopping at the Gap for Inbred Hicks. (It’s does turn out that these people are in fact inbred, but that doesn’t mean they can’t do laundry and wear a blue shirt once in a while, does it?)

But where the film really excels at failing is in its explanation for why all of this is happening. Beginning with the fairly routine “town got tired of evil guy chopping heads off kids to give him
power and priest killed him with a magic sword and left his body to rot until his head fell off” it quickly goes off the rails from there.

You will get a headache the size of which can only be cured by a visit from HH himself amidst talk of him showing up every seven years, that all the townspeople are his kids and they and the town only exist so long as he gets seven heads whenever he appears, him slowly growing his own grody head back with each head he feeds to the pool of living demonic tar in his hideout and the uncovering of where the magic sword is hidden. By the time people started talking about the constellation Hydra and how the town has the same shape as it, I figured out HH only appeared every seven years because it took that long to tell everyone what was going on!

While Headless Horseman hews too closely to everything wrong with lame slasher films (unlikable heroes, silly motivations, lack of scares, poor decision making, not enough for the town dwarfs to do) to really justify making an effort to watch it, there is a decent amount of CGI-aided gory deaths and HH romps around quite a bit while assuming a variety of looks throughout the film (headless, pumpkin-headed, and finally Red Skull-esque new head) that the completely undemanding Halloween movie aficionado might be marginally satisfied with the results. An added incentive to seek it out is for a scene where a girl hits Bull from Night Court (Richard Moll) in the leg with a hammer a few times. Top that Washington Irving!